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Villa I Cipressini Tuscany Private luxury pool spa

Photo gallery for Villa I Cipressini Tuscany Private luxury pool spa

A cozy interior with a stone staircase, a seating area with a view of the sunset, and a fireplace.
Property video
A spa area with a hot tub, a view of the outdoors, and a seating area with a chair and a table.
A dining table set for two with a view of a sunset through an arched window.
A clear blue swimming pool with a view of the countryside.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Enjoy the heated pool
    A rare find in this area - swim in comfort or have a relaxing dip.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Pienza Cathedral

Popular amenities

  • Massages in spa
  • Balcony
  • Spa pool on site
  • Private pool
  • On-site fitness centre
  • Arcade/game room

Explore the area

View map
Pienza, Siena
  • Place, Historic Centre of Pienza
    ‪18 min walk‬
  • Place, Palazzo Piccolomini
    ‪18 min walk‬
  • Place, Pienza Cathedral
    ‪19 min walk‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds

Bedroom 5

2 Single Beds

7 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Bathroom 6

Bathroom 7

Spaces

Kitchen
Balcony
Separate dining area
Garden

Add dates for prices

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10.0 out of 10, Exceptional, (1 review)
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About the area

Pienza

Pienza is home to this holiday home. Chiesa di San Francesco and Palazzo Piccolomini are local landmarks, and some of the area's activities can be experienced at Enoteca Di Ghino and Triacca Winery. Travelling with kids? Consider Art Studio di Adelina Quadri and Horti Leonini. Spend some time exploring the area's activities, including golfing.
View more Holiday homes in PienzaOpens in a new window
Map
Pienza, Siena

What's nearby

  • Historic Centre of Pienza - 18 min walk - 1.5 km
  • Palazzo Piccolomini - 18 min walk - 1.5 km
  • Pienza Cathedral - 19 min walk - 1.7 km
  • Piazza Pio II - 19 min walk - 1.7 km
  • Palazzo Vescovile - 19 min walk - 1.7 km

Getting around

  • Foiano della Chiana Station - 29 min drive

Restaurants

  • ‪Bar Il Casello - ‬3 min drive
  • ‪Trattoria La Chiocciola - ‬20 min walk
  • ‪Caffe Dante - ‬10 min drive
  • ‪Idyllium - ‬19 min walk
  • ‪Pizzeria Bar L'Officina del Gusto - ‬10 min drive

Frequently asked questions

Does Villa I Cipressini Tuscany Private luxury pool spa have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Villa I Cipressini Tuscany Private luxury pool spa pet-friendly?

Yes, this property allows pets (limit 1 total).

What time is check-in at Villa I Cipressini Tuscany Private luxury pool spa?

Check-in begins at 3:00 PM.

What time is check-out at Villa I Cipressini Tuscany Private luxury pool spa?

Checkout is at 10:00 AM.

Where is Villa I Cipressini Tuscany Private luxury pool spa located?

This family-friendly Pienza holiday home is within 1 mi (2 km) of Pieve di Corsignano, Historic Centre of Pienza and Artemisia Gallery. Palazzo Borgia and Porta al Prato are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 62 out of 62 reviews
Rating 8 - Good. 0 out of 62 reviews
Rating 6 - Okay. 0 out of 62 reviews
Rating 4 - Poor. 0 out of 62 reviews
Rating 2 - Terrible. 0 out of 62 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
If you are dreaming of the perfect Tuscan villa, look no further. This was the most beautiful property in the most beautiful location, walkable to the town of Pienza, but surrounded by vast, majestic land. Every day people routinely stopped at the side of the road to take pictures of the villa. It's postcard perfect. Thiago, the host, was incredible, there to greet us personally and answered all our questions throughout our stay. The villa itself is meticulously kept, with such attention to detail. Could not recommend this place more highly.
Stayed 8 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a wonderful week! The villa was better than expected highlights were: recently renovated bathrooms for every bedroom, the spa room with a huge hot tub to relax in after a day of touring, comfortable outdoor patio, gorgeous pool and views and an easy walk to town through fields and olive trees.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy

Lovely Stay

Beautiful villa in a beautiful setting, walkable to Pienza and overall great stay.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 6 Sept 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Leigh!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thiago was very attentive. The house was great. Pienza and surrounding area were beautiful
Stayed 6 nights in Nov 2025
Response from VrboOwner on 7 Mar 2026
Thanks for the description and compliments Tucker, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This villa was AMAZING ! Perfect luxurious accommodations.. met all of our requirements… clean , spacious, lovely frie place and outdoor grill. Bath facilities were lovely, hot water plentiful, bed so comfy. Location was PERFECT! Short walk to beautiful Pienza.. easy quick drive to beautiful Montipulciano. Our host , Thiago , was superb. One guest lost luggage and Thiago retrieved it from Florence Airport and DROVE IT TO THE VILLA!! Amazing and above and beyond.. we so enjoyed our stay and will return when possible but would recommend to my dearest friends and family to stay in this most lovely place!!
Stayed 14 nights in Mar 2026
Response from VrboOwner on 3 Apr 2026
Thank you so much for your kind words! It was a real pleasure hosting you, and I’m so glad to hear you enjoyed your stay. Knowing that you appreciated the space and the experience means a lot to me. You’re always welcome back anytime Ruth! I’d be happy to host you again in the future!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Villa I Cipressini is a special place, even to our well traveled family. The villa very comfortably suited our party of eight adults and two infants. The residence is tastefully appointed, roomy and immmaculate. Its location adjacent to Pienza is superb, and the grounds offer some of the greatest views in Toscana . Most important is the attention of Thiago to our experience. The villa check in really is seamless, with everything easily explained and immediately available. Thiago is a thoughtful and conscientious host - the smallest issue was immediately addressed. Cannot say enough about this experience. I Cipressini is a dream—exactly what one wants in a farmhouse stay.
Stayed 8 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

Stunning house and grounds. Thiago was a great communicator and arranged a chef for us one night. Just trying to figure out when we can return - thanks Thiago!
Stayed 7 nights in Jun 2022
Response from VrboOwner on 6 Sept 2023
Thank you for taking the time to share your thoughts on I Cipressini. We are happy to learn that your recent stay was an enjoyable experience and it gives us great pleasure to read your kind words. We hope to welcome you at I Cipressini soon. Best regards and many thanks David! "I Cipressini"
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Postcard perfect Tuscan family holiday

Our family group of 9 - 3 generations ages 15- 81 - had a wonderful stay at this villa. The layout was excellent - each bedroom with it’s own bathroom, large dining room with window facing the sunset and well equipped kitchen. We appreciated being able to walk into Pienza- and it is great location for exploring nearby towns. Thiago connected us to a chef - we enjoyed a cooking lesson and a gourmet meal over 2 evenings.
Stayed 7 nights in Sep 2022
Response from VrboOwner on 6 Sept 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Jane!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful spacious villa, great location, amazing pool, incredible sunsets!

Our family had a wonderful time staying at Villa I Cipressini! We had plenty of space with even a few beds to spare for our family of 5! Thiago was a wonderful host—check in and check out were a breeze, and communication was very easy and quick. The pool and spa area are top notch, and the sunsets were truly incredible. We enjoyed stayed here right in Pienza and made fun day trips to Montepulciano, Montalcino, and Siena. We will certainly try to stay here again on our next visit to Tuscany!
Stayed 5 nights in Jul 2024
Response from VrboOwner on 18 Feb 2025
Thanks for the description and compliments Christopher, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay

Communication with Thiago was great and the house is just amazing. Very close to Pienza by walk and the location is just unbelievable. Whaouuuu no critic can be done. Jacouzy, laundry, swimming pool to relax, very practical kitchen… this a dream house
Stayed 7 nights in Aug 2022
Response from VrboOwner on 6 Sept 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Marc!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Desn't get any better tha this villa!

The villa is even better than the pictures show. It is great! The proximity to Pienza - just beautiful a short walk- makes for full enjoyment of the villa and the town. Thiago, property manager, is very responsive and helpful. Our entire party was impressed and enjoyed their time at the villa.
Stayed 28 nights in May 2022
Response from VrboOwner on 6 Sept 2023
Thank you for taking the time to share your thoughts on I Cipressini. We are happy to learn that your recent stay was an enjoyable experience and it gives us great pleasure to read your kind words. We hope to welcome you at I Cipressini soon. Best regards and many thanks "I Cipressini"
Archival

10/10 Excellent

Great Place to Stay

This was our second time to stay at Il Cipressini and we plan to go again. It is a very comfortable house with fine bathrooms and a very workable kitchen. The views from the house are lovely. The owner is very accomidating and takes care of everything. The location of the house is ideal for seeing the best of and most beautiful parts of Tuscany. It is anywhere from 10 minuets to less than an hour to all the sights of Tuscany. It is located a comfortable 10 minuite walk to downtown Piensa, a very historic hilltop town which has several good restaurants. We highly recommend staying at Il Cipressi.
Response from VrboOwner on 6 Sept 2023
We are very happy when we are able to offer our guests a nice holiday. We make continuous improvements and new works to provide a holiday to remember with great pleasure. Thank you so much. Andrea & Elisabetta
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A DREAM RENTAL!!!

We were six family members aging from four years old up to 74 years old and had the time of our lives at this house! Thiago was beyond helpful and answered my WhatsApp messages throughout the whole time. We were there with various questions we adored Pienza, which was only a two minute drive away and spent quite a bit of time there. We also took day trips to Montalcino and Montepulciano. We loved and used the hot tub room more than a few times. The scenery and sunsets were incredible. Seriously a dream location! Thank you, Thiago for all your help!
Stayed 5 nights in Mar 2025
Response from VrboOwner on 13 Apr 2025
Thank you so much for your kind words! It was a real pleasure hosting you, and I’m so glad to hear you enjoyed your stay. Knowing that you appreciated the space and the experience means a lot to me. You’re always welcome back anytime — I’d be happy to host you again in the future!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home in Pienza Tuscany!!

We had a wonderful stay at I Cipressini!! The home is perfect for a large group. There were four couples and we each had a beautiful bedroom suite with amazing views of the country side. The house is immaculate and very comfortable. There are several areas to sit outside to take in the views! We enjoyed having the private chef for the evening and the wine tasting trip that Thiago arranged for us. The town of Pienza is nearby so we we’re able to walk into town for dinner. We all hope to return one day! Thank you!
Stayed 3 nights in Sep 2019
Response from VrboOwner on 6 Sept 2023
We are very pleased to be able to give our guests a fabulous vacation. We appreciate your kind review, we put maximum effort and a lot of passion. Thank you so much for how you leave the house. Hope to see you soon. Thank you Kris!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise in Pienza

The most beautiful property we have ever stayed at! The amenities at the villa were wonderful and grounds were magnificent. it was peaceful and relaxing by the pool or in the hot tub. Pienza is a 15 minute walk and is a cute little town with the nicest people, restaurants, shops, and grocery store for any essentials needed. Communication with the host, Thiago, was excellent and he was very helpful with anything we asked for. He helped us arrange a private chef at the villa for my husband's birthday which was delicious and felt like we were at a restaurant. Book this villa, you will be very happy that you did!
Stayed 7 nights in Aug 2022
Response from VrboOwner on 6 Sept 2023
Your review is stunning Maria! Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific family vacation

This was our second time staying at this amazing property. Thiago was very responsive after our booking and providing recommendations and even booking dinner reservations. The chef he recommended, Giancarlo from The Tuscan Chef, was absolutely amazing! It will be an unforgettable 85 birthday dinner. During our stay. Thiago was very responsive and is very easy to work with. The villa is just as breathtaking as we remembered. We were glad to share this trip with our spouses. Everyone was very comfortable and satisfied with their stay. The spa room was used frequently. Only regret is that we were not able to use the pool, with it’s amazing views, as much due to the cooler weather. I will definitely be returning for visit #3.
Stayed 11 nights in May 2025
Response from VrboOwner on 7 Mar 2026
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Archival

10/10 Excellent

I Ciprissini, pienza

We rented this home for 2 weeks while we took italian lessons. It was perfect!! We had our road bikes with us and there are so many rides you can do from the house. The gentleman who meets you at the house and runs the Bar il Casello in town, Paulo, was wonderful. He met us, explained the house and area and even helped us make reservations for dinner. The house is big - 3 bedrooms and 3 bathrooms. It is located a perfect distance from the town of Pienza. A short walk to town for dinner. We loved the house and the area. We would highly recommend it.
Response from VrboOwner on 6 Sept 2023
We are very pleased to be able to give our guests a fabulous vacation. We appreciate your kind review, we put maximum effort and a lot of passion. Hope to see you soon. Thank you.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Tuscan Villa

We took a trip with 6 of our friends to Tuscany for 4 days and were lucky enough to stay at this amazing villa. From the second we booked the trip, Thiago was amazing! He helped arrange wine tasting tours, a personal chef in the villa with cooking lessons and airport transfers. When we arrived he had left us a beautiful platter of cheeses and meats. The villa is truly beautiful with attention to every detail. The pictures do not do it justice. We loved everything about it, but the sunsets and views were our favorite. We plan to return and spend even more time! Thank you Thiago.
Stayed 4 nights in Apr 2023
Response from VrboOwner on 13 June 2024
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Katina!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy

Experience of a Lifetime A+++++

Experience of a lifetime. Just returned from the most amazing week at II Cipressini. Family of 5. Three adult children in their 20s. Spacious, clean, walk to town, Pienza is a gem. Time has stood still in historic downtown Pienza. Views from Villa are breathtaking. The II Cipressini hosts will steer you to home chefs, tours, restaurants etc. Great spot for families, couples, and friends to explore all the neighboring towns and wineries in Tuscany as well as Siena and Florence. Book without hesitation. Family from Westchester NY.
Stayed 7 nights in Aug 2023
Response from VrboOwner on 13 June 2024
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Laura!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place to enjoy Tuscany!

We recently returned from an amazing stay at I Cipressini. The house itself was situated right outside the town of Pienza, offering a perfect location to both walk to a charming town, but also to explore different areas of Tuscany. The house was very clean, well stocked, and the views from the house were breathtaking. There is tons of room for a group to enjoy this house. Thiago is an amazing host. He is extremely responsive both before the trip and during the stay, and is ready to help you make the most of your trip. He helped us setup a private cooking class at the house, a wine tour, and helped provide recommendations and personally secured reservations on our behalf throughout our stay. All of which made the trip special. I'm grateful to have found Thiago and this property, and highly recommend.
Stayed 4 nights in Oct 2019
Response from VrboOwner on 6 Sept 2023
Thanks for the description and compliments Bryan, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent property

We had 3 families with 6 adults & 4 children……great accommodations. …4 bedrooms & 4.5 bathrooms in the main house.& a 1 bedroom /1 bath guest cottage which was our “ grandparents “suite.We walked to Pienza every morning on the dirt path across the owner’s property; my guess is about 15 minutes ,maybe 1 km. Of course the grandchildren loved the swimming pool,especially after day trips plus the temperature was very high. The location is great for exploring Tuscany as Montepulciano is a 15 minute drive & Montalcino is 25 minutes. Thiago was most helpful & was available with quick responses to our questions. He also recommended private chefs to prepare dinners for our families; the cost was much less than going to restaurants & really enhanced our stay.
Stayed 6 nights in Jul 2022
Response from VrboOwner on 6 Sept 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much William!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unique property

The house and property are fantastic. It is perfect size for a large, multi-generational family trip. Thiago was extremely responsive before and during our stay. He helped arrange for the outstanding chef, Giancarlo from Tuscan Chef, to come to the house. He also helped arrange day trip to Florence. Montepulciano, Siena, and smaller towns are easy drive. The views are incredible, especially to the West and North. The best and most unique aspect, though, is the walking path to Pienza. The only hard part is crossing the street; once over you are walking through fields and then a shaded path to the walls of the town. Air conditioning was typical for Europe and opening the windows was often better option; they had screens.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 13 June 2024
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Michael!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Classic Beautiful Tuscan Villa

Our group of four couples had a great experience at this Villa. It was even more beautiful than the pictures. Great indoor and outdoor spaces for visiting with friends in the relaxed country side. The location is perfect for visiting Brunello focused wineries. Also a great spot for visiting nearby towns such as Montecino, Pienza, and Montepulciano. There is a pedestrian walkway with beautiful views if you don’t have a car and want to walk 20 minutes into Pienza for dinner. We also visited places like Voltara and San Gimignano by drier. Most evenings we brought in a Chef recommended by the house manager, Thiago. The cooking class at the Villa was a lot of fun for our group and the food very good. If you are staying more than two nights make sure to stop at a market on your way to the house for extra Shampoo, Coffee, and Tolite paper as stocked supplies at the house are very limited.
Stayed 5 nights in May 2023
Response from VrboOwner on 13 June 2024
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Jeffrey!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Better Than Imagined

From the very first moment we drove onto the property of I Cipressini we knew we were in for something very special! The property photos, while quite stunning in themselves, simply don't do justice to how beautiful the property is in person. The layout of the villa was easy to navigate and designed to take advantage of Tuscany's sunsets. The added bonus of having a separate one-bedroom annex building was perfect for our family as it gave our adult kids their own space while my wife and I enjoyed our privacy. The pool setting which overlooked the Tuscan valley was both a great relief from the August warmth and a great place to just hang out and enjoy Tuscany's beauty! I should note that Thiago was quite wonderful throughout the entire process, from booking to arrival, to all the other small requests/needs we had during our stay. It would be an understatement to say that I Cipressini is a wonderful villa...it is so much more!!!
Stayed 7 nights in Aug 2019
Response from VrboOwner on 6 Sept 2023
Thanks for the description and compliments Scott, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Verified review

10/10 Excellent

Everything we dreamed of!

If you have ever dreamed of renting a home in Tuscany and exploring the surrounding villages, this is your dream come true! This home is immaculate, beautiful, and comfortable. The owners are friendly, welcoming, and responsive to any needs you may have. The house is within close walking distance to Pienza, which is perfect for your morning coffee and people watching. The town is lovely! The owner referred us to a local chef who came to us for a full evening of cooking together and it was one of the highlights of our trip. There is so much to do and see within day trips of this house that we wished we had more time there instead of moving on! The owners have recently completed the addition of a beautiful Spa to the property, complete with a large window for viewing the Tuscan sunset from the jacuzzi. This lovely home is perfect for all types of groups traveling together. The bedrooms are large, the beds comfortable, AND each bedroom has its own bathroom. If we ever get opportunity, we will definitely stay here again! If you are lucky enough rent this home, you won’t be disappointed!
Stayed 4 nights in Apr 2019
Response from VrboOwner on 6 Sept 2023
Thanks for the description and compliments Cindy, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
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